CZ20032491A3 - Ftalazinonpiperidinové deriváty - Google Patents

Ftalazinonpiperidinové deriváty Download PDF

Info

Publication number: CZ20032491A3
Authority: CZ; Czechia
Prior art keywords: phenyl; tetrahydro; alkyl; substituted; phthalazin
Prior art date: 2001-02-15

Application number

CZ20032491A

Other languages

Czech (cs)

English (en)

Inventor

Armin Hatzelmann

Daniela Bundschuh

Hans-Petr Kley

Hendrik Timmerman

Johannes A. M. Christiaans

Gerhard Grundler

Beate Schmidt

Geert Jan Sterk

Original Assignee

Altana Pharma Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-02-15

Filing date

2002-02-14

Publication date

2004-01-14

2002-02-14 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2004-01-14 Publication of CZ20032491A3 publication Critical patent/CZ20032491A3/cs

Links

-1 Phthalazinone piperidine derivatives Chemical class 0.000 title claims description 182
150000001875 compounds Chemical class 0.000 claims abstract description 64
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
150000003839 salts Chemical class 0.000 claims description 28
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 27
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 25
125000004076 pyridyl group Chemical group 0.000 claims description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
125000001153 fluoro group Chemical group F* 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 6
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
150000002430 hydrocarbons Chemical class 0.000 claims description 5
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000001555 benzenes Chemical class 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
JBXODHBHAPVHDX-LEWJYISDSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(morpholine-4-carbonyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)N2CCOCC2)CC1 JBXODHBHAPVHDX-LEWJYISDSA-N 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
VBKPPDYGFUZOAJ-UHFFFAOYSA-N 5-oxopentanoic acid Chemical compound OC(=O)CCCC=O VBKPPDYGFUZOAJ-UHFFFAOYSA-N 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
NHVCANZLYPMKSR-LEWJYISDSA-N (4as,8ar)-2-(1-acetylpiperidin-4-yl)-4-(3,4-diethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(C)=O)CC1 NHVCANZLYPMKSR-LEWJYISDSA-N 0.000 claims description 2
PMSDQTJDMYHMRP-VQTJNVASSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-(1-methylsulfonylpiperidin-4-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(C)(=O)=O)CC1 PMSDQTJDMYHMRP-VQTJNVASSA-N 0.000 claims description 2
RLBQZJLGPGGCRU-BJKOFHAPSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(pyridine-4-carbonyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)C=2C=CN=CC=2)CC1 RLBQZJLGPGGCRU-BJKOFHAPSA-N 0.000 claims description 2
AMRVEJYMDSINDP-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(4-nitrophenyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C=2C=CC(=CC=2)[N+]([O-])=O)CC1 AMRVEJYMDSINDP-XZOQPEGZSA-N 0.000 claims description 2
IDSNOSDXUZNXFS-RRPNLBNLSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)CC1 IDSNOSDXUZNXFS-RRPNLBNLSA-N 0.000 claims description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
208000023504 respiratory system disease Diseases 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 5
IRQAORMVIRUVSL-IZZNHLLZSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C=CC(C)=CC=2)CC1 IRQAORMVIRUVSL-IZZNHLLZSA-N 0.000 claims 1
VUNOKMWSRYYBGQ-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(CC=2N=CC=CC=2)CC1 VUNOKMWSRYYBGQ-XZOQPEGZSA-N 0.000 claims 1
RYRAJXPFVSZNKM-LOSJGSFVSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[(2-oxochromen-7-yl)methyl]piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(CC=2C=C3OC(=O)C=CC3=CC=2)CC1 RYRAJXPFVSZNKM-LOSJGSFVSA-N 0.000 claims 1
CEDBOSAGZPVJAF-LOSJGSFVSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[[4-(thiadiazol-4-yl)phenyl]methyl]piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(CC=2C=CC(=CC=2)C=2N=NSC=2)CC1 CEDBOSAGZPVJAF-LOSJGSFVSA-N 0.000 claims 1
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
MNNXYABGSPITFF-LEWJYISDSA-N 1-[4-[(4as,8ar)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]piperidine-1-carbonyl]-4-ethylpiperazine-2,3-dione Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N1CCC(N2C([C@@H]3CC=CC[C@@H]3C(=N2)C=2C=C(OC)C(OC)=CC=2)=O)CC1 MNNXYABGSPITFF-LEWJYISDSA-N 0.000 claims 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 4
239000002587 phosphodiesterase IV inhibitor Substances 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
239000000047 product Substances 0.000 description 60
239000007858 starting material Substances 0.000 description 40
238000002844 melting Methods 0.000 description 34
230000008018 melting Effects 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
238000002425 crystallisation Methods 0.000 description 16
230000008025 crystallization Effects 0.000 description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 11
101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
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238000000034 method Methods 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
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Classifications

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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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CZ20032491A 2001-02-15 2002-02-14 Ftalazinonpiperidinové deriváty CZ20032491A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP01103496		2001-02-15

Publications (1)

Publication Number	Publication Date
CZ20032491A3 true CZ20032491A3 (cs)	2004-01-14

Family

ID=8176497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20032491A CZ20032491A3 (cs)	2001-02-15	2002-02-14	Ftalazinonpiperidinové deriváty

Country Status (22)

Country	Link
US (3)	US6953853B2 (pl)
EP (1)	EP1362044A1 (pl)
JP (1)	JP4301812B2 (pl)
KR (1)	KR20030074817A (pl)
CN (1)	CN1524080A (pl)
AU (1)	AU2002234634B2 (pl)
BG (1)	BG108124A (pl)
BR (1)	BR0207278A (pl)
CA (1)	CA2438520C (pl)
CZ (1)	CZ20032491A3 (pl)
EA (1)	EA200300836A1 (pl)
EE (1)	EE05386B1 (pl)
HR (1)	HRP20030636B1 (pl)
HU (1)	HUP0303193A3 (pl)
IL (1)	IL156812A0 (pl)
MX (1)	MXPA03007310A (pl)
NO (1)	NO325245B1 (pl)
NZ (1)	NZ527424A (pl)
PL (1)	PL363391A1 (pl)
SK (1)	SK11382003A3 (pl)
WO (1)	WO2002064584A1 (pl)
ZA (1)	ZA200306815B (pl)

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WO2004018450A1 (en) *	2002-08-10	2004-03-04	Altana Pharma Ag	Piperidine-n-oxide-derivatives
WO2004062671A2 (en) *	2003-01-14	2004-07-29	Altana Pharma Ag	Pde4 inhibitors for the treatment of neoplasms of lymphoid cells
WO2004098633A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde-4 inhibitor and a tnf alpha antagonist
WO2004098578A2 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde4 inhibitor and a tnf-alfa antagonist selected from infliximab, adalimumab, cdp870 and cdp517
WO2004098606A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Composition comprising a pde4 inhibitor and shuil-1r ii
WO2004098605A1 (en) *	2003-05-12	2004-11-18	Altana Pharma Ag	Pharmaceutical composition comprising a pde4 inhibitor and il-1 trap
EA012279B1 (ru) *	2003-05-22	2009-08-28	Никомед Гмбх	Композиция, включающая ингибитор pde4 и ингибитор pde5
WO2005023253A1 (en) *	2003-09-05	2005-03-17	Altana Pharma Ag	Use of pde4 inhibitors for the treatment of diabetes mellitus
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EP1716133B1 (en)	2004-02-04	2008-03-26	Nycomed GmbH	2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors
AU2006222060B2 (en)	2005-03-08	2011-09-01	Takeda Gmbh	Roflumilast for the treatment of diabetes mellitus
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EP2359826B1 (en)	2006-07-05	2013-10-30	Takeda GmbH	Combination of HMG-COA reductase inhibitor rosuvastatin with a phosphodiesterase 4 inhibitor, such as roflumilast, roflumilast-N-oxide for the treatment of inflammatory pulmonary diseases
ATE459358T1 (de) *	2006-12-20	2010-03-15	Glaxo Group Ltd	4-benzyl-1(2h)-phthalazinone als h1-rezeptor- antagonisten
CA2686909C (en)	2007-05-16	2016-07-05	Nycomed Gmbh	Pyrazolone derivatives as pde4 inhibitors
AR074318A1 (es)	2008-11-14	2011-01-05	Nycomed Gmbh	Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias.
AU2012269133A1 (en) *	2011-06-17	2014-01-30	Takeda Gmbh	Novel phthalazinone-pyrrolopyrimidinecarboxamide derivatives
WO2013106547A1 (en)	2012-01-10	2013-07-18	President And Fellows Of Harvard College	Beta-cell replication promoting compounds and methods of their use
EP3165224A1 (en)	2015-11-09	2017-05-10	Albert-Ludwigs-Universität Freiburg	Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders
JP6820717B2 (ja)	2016-10-28	2021-01-27	株式会社日立ハイテク	プラズマ処理装置
CN113121417A (zh) *	2019-12-30	2021-07-16	苏州盛迪亚生物医药有限公司	一种新型哌啶衍生物及其药物用途
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EE05386B1 (et) *	2001-02-15	2011-02-15	ALTANA�Pharma�AG	Ftalasinoon-piperidinoderivaadid,ÁnendeÁkasutamineÁjaÁravim
CZ20033205A3 (en)	2001-04-25	2004-03-17	Altana Pharma Ag	Piperazino-derivatives and their use as pde4 inhibitor
NZ529221A (en)	2001-04-25	2005-04-29	Altana Pharma Ag	Phthalazinones with PDE-inhibiting properties for treatment of airway disorders and other inflammatory conditions
WO2004018450A1 (en)	2002-08-10	2004-03-04	Altana Pharma Ag	Piperidine-n-oxide-derivatives
WO2004018451A1 (en)	2002-08-10	2004-03-04	Altana Pharma Ag	Pyridazinone-derivatives as pde4 inhibitors
CA2494613C (en)	2002-08-10	2011-06-28	Altana Pharma Ag	Pyrrolidinedione substituted piperidine-phthalazones as pde4 inhibitors

2002
- 2002-02-14 EE EEP200300311A patent/EE05386B1/xx not_active IP Right Cessation
- 2002-02-14 CN CNA02805038XA patent/CN1524080A/zh active Pending
- 2002-02-14 CA CA2438520A patent/CA2438520C/en not_active Expired - Fee Related
- 2002-02-14 NZ NZ527424A patent/NZ527424A/en not_active IP Right Cessation
- 2002-02-14 BR BR0207278-5A patent/BR0207278A/pt not_active IP Right Cessation
- 2002-02-14 MX MXPA03007310A patent/MXPA03007310A/es active IP Right Grant
- 2002-02-14 US US10/467,832 patent/US6953853B2/en not_active Expired - Fee Related
- 2002-02-14 KR KR10-2003-7010552A patent/KR20030074817A/ko not_active Withdrawn
- 2002-02-14 SK SK1138-2003A patent/SK11382003A3/sk unknown
- 2002-02-14 PL PL02363391A patent/PL363391A1/pl unknown
- 2002-02-14 AU AU2002234634A patent/AU2002234634B2/en not_active Ceased
- 2002-02-14 IL IL15681202A patent/IL156812A0/xx unknown
- 2002-02-14 EA EA200300836A patent/EA200300836A1/ru unknown
- 2002-02-14 JP JP2002564515A patent/JP4301812B2/ja not_active Expired - Fee Related
- 2002-02-14 WO PCT/EP2002/001547 patent/WO2002064584A1/en not_active Ceased
- 2002-02-14 HU HU0303193A patent/HUP0303193A3/hu unknown
- 2002-02-14 CZ CZ20032491A patent/CZ20032491A3/cs unknown
- 2002-02-14 HR HRP20030636AA patent/HRP20030636B1/xx not_active IP Right Cessation
- 2002-02-14 EP EP02701277A patent/EP1362044A1/en not_active Withdrawn
2003
- 2003-08-14 NO NO20033618A patent/NO325245B1/no not_active IP Right Cessation
- 2003-08-21 BG BG108124A patent/BG108124A/bg unknown
- 2003-09-01 ZA ZA200306815A patent/ZA200306815B/en unknown
2005
- 2005-06-03 US US11/143,721 patent/US7179810B2/en not_active Expired - Fee Related
2006
- 2006-12-29 US US11/647,191 patent/US7531540B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO325245B1 (no)	2008-03-10
EE200300311A (et)	2003-10-15
BR0207278A (pt)	2004-02-10
US6953853B2 (en)	2005-10-11
EP1362044A1 (en)	2003-11-19
MXPA03007310A (es)	2003-12-04
PL363391A1 (pl)	2004-11-15
SK11382003A3 (sk)	2004-01-08
HRP20030636B1 (en)	2012-05-31
EA200300836A1 (ru)	2004-02-26
CA2438520A1 (en)	2002-08-22
US7531540B2 (en)	2009-05-12
CA2438520C (en)	2011-10-04
KR20030074817A (ko)	2003-09-19
NZ527424A (en)	2005-02-25
IL156812A0 (en)	2004-02-08
BG108124A (bg)	2004-08-31
US7179810B2 (en)	2007-02-20
US20040067946A1 (en)	2004-04-08
AU2002234634B2 (en)	2007-07-26
WO2002064584A1 (en)	2002-08-22
ZA200306815B (en)	2004-06-17
EE05386B1 (et)	2011-02-15
HRP20030636A2 (en)	2005-06-30
CN1524080A (zh)	2004-08-25
US20050234062A1 (en)	2005-10-20
NO20033618L (no)	2003-10-15
NO20033618D0 (no)	2003-08-14
JP2004518727A (ja)	2004-06-24
HUP0303193A3 (en)	2007-08-28
HUP0303193A2 (hu)	2003-12-29
US20070129373A1 (en)	2007-06-07
JP4301812B2 (ja)	2009-07-22

Publication	Publication Date	Title
CZ20032491A3 (cs)	2004-01-14	Ftalazinonpiperidinové deriváty
JP4555684B2 (ja)	2010-10-06	Ｐｄｅ４阻害剤としての、ピロリジンジオンにより置換されたピペリジン−フタラゾン
JP2005538137A (ja)	2005-12-15	ピペリジン−ｎ−オキシド誘導体
JP2005538138A (ja)	2005-12-15	Ｐｄｅ４インヒビターとしてのピリダジノン誘導体
AU2002234634A1 (en)	2003-02-20	Phthalayinone-piperidino-derivatives as PDE4 inhibitors
CZ196A3 (en)	1996-06-12	Substituted benzamides, process of their preparation and pharmaceutical compositions containing thereof
CZ20033206A3 (cs)	2004-02-18	Nové ftalazinony
KR20020043238A (ko)	2002-06-08	Ｐｄｅ４ 억제제로서의 테트라히드로티오피란프탈라지논유도체
AU2002315311B2 (en)	2007-12-06	Piperazino-derivatives and their use as PDE4 inhibitor
EP1228046B1 (en)	2007-09-26	Phthalazinone derivatives as pde 4 inhibitors
JPH09510992A (ja)	1997-11-04	ブラジキニンアンタゴニストとしてのジヒドロピリジン誘導体
JPH04244081A (ja)	1992-09-01	１，４−ジヒドロピリジン誘導体およびそれを有効成分とするアレルギー性または炎症性疾患治療剤